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Eschenmoser-Claisen Rearrangement

Sandmeyer reaction   Named Reactions in Organic Synthesis

Reaction category:
Pericyclic and photochemical reactions

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In 1964 the Swiss chemist Albert Eschenmoser reported that allylic or benzylic alcohols heated in the presence of N,N-dimethylacetamide dimethyl acetal in xylenes underwent a form of Claisen rearrangement. This generated a γ,δ-unsaturated amide with a high level of stereospecificity, and today this transformation has become known as the Eschenmoser - Claisen rearrangement.

This rearrangement typically occurs at lower temperatures, between 100-150 degrees centigrade, than other variants such as the Claisen rearrangement itself and is more (E) - selective.

During the first total synthesis of (±)-Stenine by D.J.Hart and colleagues, one of the key steps was an Eschenmoser - Claisen rearrangement that afforded a key amide intermediate in 93% yield.

 

Mechanism of the Eschenmoser-Claisen rearrangement:


mechanism of the Eschenmoser-Claisen rearrangement
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Other reaction categories:

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle-formation

Transition metal-catalyzed couplings

Oxidation

Reactions involving carbonyl compounds

Reduction reactions

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Electrophilic addition reactions


Some relevant Alfa Aesar products for the Eschenmoser-Claisen rearrangement:

N,N-Dimethylacetamide dimethyl acetal, tech. 90%, stab with 5-10% methanol
Xylenes, mixed, 97+%
Xylenes, ACS, 98.5+% (Assay, isomers plus ethylbenzene


We have many allylic and benzylic alcohols in our portfolio.

 

 

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